2,5-Furan-dicarboxylic acid (FDCA) has large potential to become a bio-based alternative for terephthalate in the production of polyesters such as PET. As such and for other reasons FDCA was identified as one of the Top-12 priority chemicals in the DOE report on Top Value-Added Chemicals from Biomass (Top Value-Added Chemicals from Biomass, Volume I—Results of screening for potential Candidates from Sugars and Synthesis gas, Department of Energy (USA), 2004). This compound may be obtained by oxidation of 5-hydroxymethylfurfural (HMF), which can be produced by heating hexose sugars under acid conditions. The DOE report discloses on page 27, some potential utilities for FDCA. These include a role as substrate for the production of succinic acid, 2,5-bis(aminomethyl)-tetrahydrofuran, 2,5-dihydroxymethyl-tetrahydrofuran, 2,5-dihydroxymethylfuran and 2,5-furandicarbaldehyde. Although the production of FDCA by chemical oxidative dehydration of C6 sugars and uses of FDCA are well known and poses technical barriers indicated in table 13 on page 26, for biotransformation—possibly enzymatic conversions—the position was unknown.
A process for the enzymatic preparation of FDCA is given in WO2009/023174. In this disclosure, a hydroxymethylfurfural species is oxidised with a chloroperoxidoreductase and hydrogen peroxide oxidised products having a carboxylic acid group at the C1 position of the hydroxymethylfurfural, in particular formylfuran carboxylic acid or FFCA. Results are e.g. shown in FIG. 1. In another embodiment, HMF is contacted with an oxidoreductase in the presence of an oxidizing substrate, whereby HMF is oxidized to at least one of diformylfuran or formylfuran carboxylic acid.
Disadvantages of the known process in WO2009/023174 are that the reaction requires hydrogen peroxide and that the product formed is a mixture of FDCA with two contaminating byproducts, hydroxymethylfuran carboxylic acid (HmFCA) and formylfuran carboxylic acid (FFCA). Consequently the yield of FDCA from HMF is reduced and additional recovery steps are needed to obtain FDCA in a substantially purified form.
In database EBI, Uniprot B2T4R9, a sequence of 577 aminoacids was identified that was inferred from homology as Glucose-Methanol-Choline oxidoreductase in the “complete sequence of chromosome 1 of Burkholderia phytofirmans PsJN.”.
In database EBI, Uniprot B2JSZ0, a sequence of 576 aminoacids was identified that was inferred from homology as Glucose-Methanol-Choline oxidoreductase in the “complete sequence of plasmid 1 of Burkholderia phymatum STM815.”.
In Deurzen, M. P. J. et al, J. Carbohydrate Chemistry 16(3), 299-309 (1997), the chloroperoxidase-catalysed oxidation of 5-Hydroxymethylfurfural is disclosed. The reaction proceeds with 60-74% selectivity to furan-2,5-dicarboxaldehyde (FDC). Byproducts were 5-hydroxymethyl-2-furancarboxylic acid (HFCA) and 5-formylfuran-2-carboxylic acid (FFCA).